View 0 Trebo Road Chester, VT MLS# 5102503
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1 of 12
$149,000
Studio

Beds

0.0

Baths

0 Trebo Road

Chester, VT

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Courtesy of ENGEL & VOLKERS OKEMO
View 302 Davidson Hill Road Chester, VT MLS# 5102316
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1 of 27
OPEN HOUSE: Sunday 8/9 1:00 PM - 3:00 PM
$359,000
2

Beds

1.0

Baths

900

Sq.Ft.

302 Davidson Hill Road

Chester, VT

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Courtesy of VERMONT REAL ESTATE COMPANY
View 3781 Flamstead Road Chester, VT MLS# 5102142
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1 of 60
$250,000
3

Beds

2.0

Baths

1,500

Sq.Ft.

3781 Flamstead Road

Chester, VT

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Courtesy of EXP REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 3781 Flamstead Road Chester, VT MLS# 5102143
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1 of 59
$250,000
Studio

Beds

0.0

Baths

3781 Flamstead Road

Chester, VT

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Courtesy of EXP REALTY
View 641 Depot Street Chester, VT MLS# 5100719
Save 641 Depot Street Chester, VT MLS# 5100719
1 of 18
$175,000
3

Beds

1.1

Baths

1,379

Sq.Ft.

641 Depot Street

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 427 Depot Street Chester, VT MLS# 5100755
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1 of 22
$100,000
Studio

Beds

0.0

Baths

427 Depot Street

Chester, VT

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Courtesy of KW COASTAL AND LAKES & MOUNTAINS REALTY/HANOVER
View 734 Gould Road Chester, VT MLS# 5100498
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1 of 15
$79,900
Studio

Beds

0.0

Baths

734 Gould Road

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 39 S Main Street Chester, VT MLS# 5100522
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1 of 9
$285,000
1,802

Sq.Ft.

39 S Main Street

Chester, VT

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Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
View 00 Quarry Road Chester, VT MLS# 5098347
Save 00 Quarry Road Chester, VT MLS# 5098347
1 of 19
$229,000
Studio

Beds

0.0

Baths

00 Quarry Road

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1372 Potash Brook Road Chester, VT MLS# 5098053
Save 1372 Potash Brook Road Chester, VT MLS# 5098053
1 of 22
$199,000
2

Beds

1.0

Baths

732

Sq.Ft.

1372 Potash Brook Road

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 3668 VT Route 103 North Chester, VT MLS# 5097620
Save 3668 VT Route 103 North Chester, VT MLS# 5097620
1 of 38
$249,500
4

Beds

2.1

Baths

1,922

Sq.Ft.

3668 VT Route 103 North

Chester, VT

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Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 3668 VT Route 103 North Chester, VT MLS# 5097621
Save 3668 VT Route 103 North Chester, VT MLS# 5097621
1 of 38
$249,500
4

Beds

3.0

Baths

1,922

Sq.Ft.

3668 VT Route 103 North

Chester, VT

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Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
View 145 South Main Street Chester, VT MLS# 5097411
Save 145 South Main Street Chester, VT MLS# 5097411
1 of 10
$385,000
3,608

Sq.Ft.

145 South Main Street

Chester, VT

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Courtesy of NANCY JENKINS REAL ESTATE
View 0 Linden Way Chester, VT MLS# 5093908
Save 0 Linden Way Chester, VT MLS# 5093908
1 of 22
$85,000
Studio

Beds

0.0

Baths

0 Linden Way

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View 00 Snell Road Chester, VT MLS# 5094246
Save 00 Snell Road Chester, VT MLS# 5094246
1 of 14
$87,500
Studio

Beds

0.0

Baths

00 Snell Road

Chester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1144 Potash Brook Road Chester, VT MLS# 5093286
Save 1144 Potash Brook Road Chester, VT MLS# 5093286
1 of 17
$75,000
2

Beds

1.0

Baths

620

Sq.Ft.

1144 Potash Brook Road

Chester, VT

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Courtesy of BUFFUM REALTY
View 250 Fenton Road Chester, VT MLS# 5090458
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Save 250 Fenton Road Chester, VT MLS# 5090458
1 of 32
$138,000
Studio

Beds

0.0

Baths

250 Fenton Road

Chester, VT

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Courtesy of EXP REALTY
View 397 River Street Chester, VT MLS# 5087965
Save 397 River Street Chester, VT MLS# 5087965
1 of 41
$325,000
4

Beds

3.0

Baths

3,332

Sq.Ft.

397 River Street

Chester, VT

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Courtesy of CUMMINGS & CO
View 663 Depot Street Chester, VT MLS# 5086202
Save 663 Depot Street Chester, VT MLS# 5086202
1 of 51
$390,000
3

Beds

2.0

Baths

1,304

Sq.Ft.

663 Depot Street

Chester, VT

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Courtesy of REAL BROKER LLC
View 508 Mattson Road Chester, VT MLS# 5082636
Save 508 Mattson Road Chester, VT MLS# 5082636
1 of 12
$99,999
Studio

Beds

0.0

Baths

508 Mattson Road

Chester, VT

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Courtesy of CUMMINGS & CO

About Chester

Listings in Chester, VT

48

Estimated median home price

$277,500
Chester VT Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chester, Vermont real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chester, VT.

Homes for Sale by Price in Chester, VT

Price Count
$0 - 100K 8
$100K - 200K 9
$200K - 300K 10
$300K - 400K 5
$400K - 500K 5
$500K - 600K 1
$600K - 700K 4
$700K - 800K 2
$800K - 900K 0
$900K - 1M 1
$1M - Max 3

Homes for Sale by Type in Chester, VT

Property Type Count
Single Family 24
Townhouse 0
Condo 0
Commercial 5
Rental 2
Lots and Land 16
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 1
Farms 0

(Data as of 8/4/2026)

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Information deemed reliable but not guaranteed.

“Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 8/6/2026”

Trends Information provided by ATTOM Data Solutions.